How to Do It

I Worry I’m About to Break the Oldest Rule in the Book When It Comes to Men and Sex

Maybe I’m fooling myself.

Man holding a phone, with an illustration of a neon texting bubble above it
Photo illustration by Slate. Photo by Alikaj2582/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I’m a 52-year-old woman previously in a sexless marriage. I finally put myself on a dating site in February to see if I could do something about my perpetual horniness, because it’d been years since I’d gotten laid. Last week I matched with a 55-year-old man who swiped right because I listed “lots of great sex” as being important in a relationship. After some initial small talk, in which I found out that he’d had similar issues in his marriage and gone a few years without sex, the texting turned to sexting, and we decided to meet to see if we liked each other. Well, we did, and went to his place—and oh my God did we do it! It was hot and sensual and I had forgotten how much fun sex could be (it was always a chore with my ex, when he wasn’t rejecting and shaming me for wanting it). He seemed to feel the same based on his comments and noises, and he did some new things to me that I loved. We both said, during and after, we wanted to meet again. Later that day, I messaged to thank him for a great afternoon, mentioned I was more turned on than before, and in case I hadn’t been clear, I wanted to get together again. He said I was awesome and wanted that too, and we had a little more dirty talk about what we’d do to each other before signing off for the day.

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Now it’s been a week, and there’s been no suggestion from him of when we can get together again. He’s sent one or two quick messages to say “sorry, busy day,” things like that. Now all I can think of is the “He’s Just Not That Into You” episode of Sex and the City, when Berger tells Carrie and her friends that if a guy is really into you he’ll do what it takes to make plans to see you again no matter what. I know this guy owns a business that’s very busy right now, but I really want to go at it again. And now I feel like a ridiculous 22-year-old girl going over my date with friends in excruciating detail to try to figure out what he really meant—which I hate!

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What’s the etiquette here? Am I too impatient? Do I hang back and wait for a busy guy to make the next invitation? Or can I go ahead and ask when he’d like to screw again, while saying if he’s changed his mind to let me know so we can unmatch? Both our profiles said we are looking for something casual, so we are on the same page there. I don’t think he was lying about getting together again or how much he enjoyed himself. But maybe I’m fooling myself?

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—Insecure and Frustrated

Dear Frustrated,

It seems like waiting for this guy is preventing you from pursuing other sexual partners. Unless specifically discussed, there’s no need for monogamy after one sexual encounter. You could be putting your desire to connect into matching with and meeting other people while you practice patience with regard to this particular partner.

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He’s in contact, if brief. So it seems reasonable to take him at face value when he says he’s interested but busy. Given the framing of “casual,” I wouldn’t push to set a date to meet again.

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As for your feelings, you haven’t dated in a while. This is all new again, and heady, and—at times—stressful. Take some deep breaths, and remember back on how you’ve processed other uncomfortable emotions. Does writing help? Do you have a friend who is good at listening and asking questions that help you get at the core of what’s going on? How about showers or walking as you think? Whatever it is, do it. You’ll get better at managing as you go.

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Dear How to Do It,

My current partner has a penis that could be a ruler. No curve, just sticks out at 90 degrees. And he’s great! But a lot of the positions I’d enjoyed with previous partners (like spooning or doggy style) don’t seem to be working out for us, angle-wise. He didn’t have a lot of experience before we got together, so he’s not sure what works other than variations on missionary or girl on top. Any suggestions?

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—Yardstick

Dear Yardstick,

Doggy is probably doable. Presuming your vagina tilts toward your tailbone slightly, you can position your body so your pelvis is curled slightly under. If you curl further under you might feel a significant amount of front wall situation, which is great if you like it and to be avoided if you don’t. You can hold this position yourself or be draped over something like the arm of a couch. Then it’s up to him to widen or narrow his stance as needed so that his penis is at the level of your vulva. Girl on top should also work if you’re upright or even leaned backward some. You might brace your hands on the meat just above his knees for balance and support. You can also probably manage a side spoon if you’re bent way forward, about 90 degrees.

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Mostly, you’ll figure out what works for the specific combination of your two bodies by experimenting. Make a game of it if you enjoy being silly, or sip tea while considering the spatial geometry of the whole thing.

Dear How to Do It,

I haven’t been in a relationship in 10 years, which I was fine with. Recently, I started casually hooking up with a friend of a friend who I’ve known for a couple of years. The thing is that I’m not particularly attracted to him—but the sex is still pretty good. In the past 10 years, I guess I’ve learned a lot about sex, and it’s about 10 times better than it was in my early 20s. And ever since I started hooking up with this guy, I’ve been really horny. Now I’m really curious about sex with other people. I’ve always thought I was a fairly responsible person, but I’ve been engaging in some unprotected sex with this guy. I’m worried that my increase in libido is going to get me into trouble. I’ve never had much casual sex, but I have this strange feeling like I’m about to go on this sexual bender. In general this doesn’t bother me except for the fact that I feel like I’ve been making poor decisions in bed and I will make a lot of poor decisions in picking these guys. I’ve been feeling very cooped up lately and would take any excuse to get out right now. Should I try to stop myself or just lean in?

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—Bendering Over

Dear Bendering Over,

I’m alarmed to see you write most of a medium-sized paragraph without acknowledging your own agency—not until the very last line. We can’t control what turns us on or what we desire, but we can absolutely strive to control our actions. If the situation really is such that you’re uncertain of your ability to stop yourself from actions you feel are risky, especially actions that you’re describing as “poor decisions,” get yourself to a psychiatrist right now. Not a therapist who wants to spend two sessions mapping your family and friend circles, but a psychiatrist who can evaluate you for psychiatric conditions that cause compulsive behavior. Large stressors—like a pandemic—have a way of bringing mental health vulnerabilities to the foreground, and it’s crucial that you make this your top priority.

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Since I’m hoping that isn’t the case and that you’re indulging in poetic license, let’s work on solutions that aren’t poor sex decisions. You feel cooped up: There are a multitude of activities you can engage in out in the world without taking sexual risks. You’re feeling sexually aroused: There’s a whole world of solo stimulation at your fingertips. If you’re struggling to make a decision about which path to pursue, flip a coin. If you know what direction you want to go but don’t want to thoroughly evaluate the activities or toys available, use random selection again. Whether you go to the park or a museum or buy an anal plug or a mini vibrator isn’t that serious of a choice. Get out there, or in there, and entertain yourself.

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Dear How to Do It,

I’m a 28-year-old bisexual woman. I had a terrible experience when I was a teenager when my mom found out I was physically intimate with another girl. My dad was a textbook conservative homophobe. That, in addition to other experiences with bi erasure, led me to ignore or stifle my attraction to other women. I’ve never had either a prolonged romantic relationship with another woman or extensive sexual experiences with them. Every time I start talking to a girl, I stop, because I feel so ridiculous not having any experience. I need to know how to communicate with my female partners about this and approach these situations with confidence. I also need to learn how to, you know, have sex with women.

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I’m outgoing, love to socialize, have a successful career, and am considered conventionally attractive. Being bashful about sex isn’t really in my vocabulary, and yet I get so embarrassed by the fact that I am basically a virgin when it comes to sex with women that I just freeze up and run away. Like, hello?! Who’s into virgins? I also fear someone will reject me when they learn I’m a virgin. I know that’s kind of a “responsibility” to shoulder, so I also struggle with when to tell prospective partners about this. I want to learn, but I feel bad or weird when I’m out with a woman and the moment comes for me to say “Hey, you have to teach me everything.”

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Am I doomed to repeat that horrible, awkward sex I had when I was learning how to act with male bodies? How do you put on a strap-on? Is there a Lesbian Sex for Dummies book? What about good porn sites for actually real lesbian sex? How do I talk to partners about this in a way that is genuine but that won’t be a huge turn-off? How do I deal with giving up my coffin-tip nails? Help!

—Figuring It Out

Dear Figuring It Out,

Let’s get to the nails first, as I’m overjoyed to tackle a sex styling question. You don’t have to give up your nails at all—many sex workers have them, and I’ve had non-professional friends who keep their nails long and use an abundance of caution. But there might be a learning curve. You can go with a more rounded and shorter shape, like squoval or round tips. Or you can keep seven or eight long nails, with the two on your dominant hand that you’re most likely to use for insertion and your thumb, if you think you’ll incorporate it, short but decorated the same way as the long ones. This has an additional effect of telegraphing to potential partners that you are prepared to put your fingers in delicate places, which might encourage them to start a conversation. And, lastly, you could keep your natural nails trimmed short, attach press-ons with the sticker tabs, and pop them off easily when you’re beginning foreplay. (There’s also a learning curve with sticker tabs, and glue isn’t as functional, as the dried residue left on nail beds can be jagged.)

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What exactly is a virgin? We have different ideas of where the boundary is. Some people claim to be re-virginized, and some see the hymen as the seal of a woman’s value. The salient point is that you’ll be figuring out how to put your anatomical knowledge into practice, and that’s what you’ll want to communicate. Each date will go differently, so you’ll have to feel out a good time to bring up the subject. You might miss your window, and you might startle people by broaching it early. Think about what you want to say, write it down, and rehearse it a few times. Maybe this is while you’re looking in the mirror, maybe this is with a trusted friend. “I have a little experience expressing attraction to other women” or “I’m not sure how to flirt with another femme” or even “This is my second time at a queer party.” If you’re near New York City, one of Vonka Romanov’s Femme Flirt workshops might be useful. If you’re somewhere else, you can look for similar sex-positive events in your area online and at sex shops. Allison Moon and K.D. Diamond’s Girl Sex 101 is a solid primer and may be the Lesbian Sex for Dummies that you seek. It addresses many of your concerns, like flirting and the mechanics of sex. Autostraddle has several other recommendations, in case you want to keep reading.

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When you’re thinking about making moves, keep in mind that you’ve got a two-decade head start on getting to know types of non-sexual body language and facial expressions of women in your area. You also may never have cause to wear a strap-on (or fist, or any other act)! You also might try it and love it, or feel neutral but pull one out for a partner who requests it. You don’t have to do anything you don’t want to. If you want to try a strap-on, you’ll want a base that is solid and holds the phallus erect. (I like SpareParts Tomboi harnesses, but the manufacturer of your penis is a great place to start if you aren’t sure which harness to go with.) From there, it’s all about taking things slow and getting to know your new appendage. At the very least, spend some time hanging out at home with it on. Get used to the wobble. Get used to how big it is. Maybe do some dancing, with pelvic thrusts. Take your time and communicate thoroughly with your partner. Good luck.

—Stoya

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